A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful βand γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.
Herein, we report
a new electrochemical method for alkoxy radical
generation from alcohols using a proton-coupled electron transfer
(PCET) approach, showcased via the deconstructive functionalization
of cycloalkanols. The electrochemical method is applicable across
a diverse array of substituted cycloalkanols, accessing a broad range
of synthetically useful distally functionalized ketones. The orthogonal
derivatization of the products has been demonstrated through chemoselective
transformations, and the electrochemical process has been performed
on a gram scale in continuous single-pass flow.
<div>
<div>
<div>
<p>A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This
electrochemical method provides access to alkoxy radicals from
alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically
useful β- and γ-chlorinated ketones (40 examples). Furthermore,
the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on
gram scale.
</p>
</div>
</div>
</div>
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.